5-dodecyl-1,3-di(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione | 1286745-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-dodecyl-1,3-di(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• 英文别名: 1,3-bis(thien-2-yl)-5-(n-dodecyl)thieno[3,4-c]pyrrole-4,6-dione；1,3-di(thien-2-yl)-5-dodecylthieno[3,4-c]pyrrole-4,6-dione；5-Dodecyl-1,3-dithiophen-2-ylthieno[3,4-c]pyrrole-4,6-dione；5-dodecyl-1,3-dithiophen-2-ylthieno[3,4-c]pyrrole-4,6-dione
• CAS: 1286745-52-5
• 化学式: C₂₆H₃₁NO₂S₃
• 分子量: 485.736
• InChiKey: XMOQHGALMAOXLB-UHFFFAOYSA-N

物化性质

• 沸点：
  597.8±50.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-dodecyl-1,3-di(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 在 溴 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以77%的产率得到1,3-bis(5-bromothiophen-2-yl)-5-(n-dodecyl)thieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Thieno[3,4-c]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors

  摘要：

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.

  DOI：

  10.1021/ja205398u
• 作为产物：
  描述：

  3,4-噻吩二羧酸酐 在 palladium diacetate 、 caesium carbonate 、 溶剂黄146 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 5-dodecyl-1,3-di(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
  参考文献：
  名称：

  FromCore和FromEnd Direct C ？H芳基化：合成Thieno [3,4-c]吡咯-4,6-二酮（TPD）-掺入D-π-A-π-D功能性低聚芳基化合物的新合成方法

  摘要：

  与此相反的传统多步合成，本文中的高效和少数步骤新的合成策略是证明了通过顺序直接C中容易制备的有机电子重要d-π-A-π-d型oligoaryls  ħ芳基化。该方法学表明，以噻吩并[3,4- c ]吡咯-4,6-二酮（TPD）或呋喃并[3,4- c ]吡咯-4,6-二酮（FPD）为中心的目标分子的合成可以从核心结构（受体）或末端结构（供体）经济地步入，这为π功能小分子半导体材料的制备提供了更灵活，更简洁的新合成替代品。另外，检查了合成的低聚芳基的光学和电化学性质。

  DOI：

  10.1002/chem.201501015

文献信息

• Synthesis and Characterization of New Thieno[3,4-c]pyrrole-4,6-dione Derivatives for Photovoltaic Applications
  作者：Ahmed Najari、Serge Beaupré、Philippe Berrouard、Yingping Zou、Jean-Rémi Pouliot、Charlotte Lepage-Pérusse、Mario Leclerc

  DOI：10.1002/adfm.201001771

  日期：2011.2.22

  A new class of low‐bandgap copolymers based on benzodithiophene (BDT) and thieno[3,4‐c]pyrrole‐4,6‐dione (TPD) units is reported. Chemical modifications of the conjugated backbone promote both high molecular weights and processability while allowing for tuning of the electronic properties. Copolymers with substituted thiophene spacers (alkyl chains facing the BDT unit) or unsubstituted thiophene spacers

  报道了一种基于苯并二噻吩（BDT）和噻吩并[3,4-c]吡咯-4,6-二酮（TPD）单元的新型低带隙共聚物。共轭主链的化学修饰既提高了分子量，又提高了可加工性，同时可以调节电子性能。具有取代的噻吩间隔基（面向BDT单元的烷基链）或未取代的噻吩间隔基的共聚物由于活性层的不良形态而往往具有较低的功率转换效率（PCE小于1％），而具有取代的噻吩间隔基（烷基链）的共聚物面向TPD单元）显示出增强的形态，PCE高达3.9％。最后，没有任何噻吩间隔基的BDT-TPD共聚物仍然表现出最佳性能，功率转换效率高达5.2％。
• NOVEL PHOTOACTIVE POLYMERS
  申请人：Leclerc Mario

  公开号：US20130048075A1

  公开（公告）日：2013-02-28

  Photoactive polymers comprising first and second co-monomer repeat units, the first co-monomer repeat unit comprising a moiety selected from the group consisting of an alkylthieno[3,4-c]pyrrole-4,6-dione moiety and a 1,3-dithiophene-5-alkylthieno[3,4-c]pyrrole-4,6-dione moiety, and the second co-monomer repeat unit comprising a moiety selected from the group consisting of a 4,4′-dialkyl-dithieno[3,2-b:2′3′-d]silole moiety, an ethylene moiety, a thiophene moiety, an N-alkylcarbazole moiety, an N-(1-alkyl)dithieno[3,2-b:2′3′-d]pyrrole moiety and a 4,8-dialkyloxylbenzo[1,2-b:3,4-b]dithiophene moiety are described herein. These polymers are suitable for use in photovoltaic cells and field effect transistors.

  本文描述了包含第一和第二共聚单体重复单元的光致聚合物，其中第一共聚单体重复单元包括从羧基[3,4-c]吡咯-4,6-二酮基团和1,3-二硫杂吡咯-5-烷基[3,4-c]吡咯-4,6-二酮基团中选择的基团，而第二共聚单体重复单元包括从4,4'-二烷基-二硫杂吡咯[3,2-b:2'3'-d]硅烷基团、乙烯基团、噻吩基团、N-烷基咔唑基团、N-(1-烷基)二硫杂吡咯[3,2-b:2'3'-d]吡咯基团和4,8-二烷氧基苯并[1,2-b:3,4-b]二噻吩基团中选择的基团。这些聚合物适用于光伏电池和场效应晶体管。
• US8816035B2
  申请人：——

  公开号：US8816035B2

  公开（公告）日：2014-08-26
• From-Core and From-End Direct CH Arylations: A Step-Saving New Synthetic Route to Thieno[3,4-<i>c</i>]pyrrole-4,6-dione (TPD)-Incorporated D--π-A-π-D Functional Oligoaryls
  作者：Po-Han Lin、Kuan-Ting Liu、Ching-Yuan Liu

  DOI：10.1002/chem.201501015

  日期：2015.6.8

  contrast to the traditional multistep synthesis, herein an efficient and fewer‐steps new synthetic strategy is demonstrated for the facile preparation of organic‐electronically important D–π–A–π–D‐type oligoaryls through sequential direct CH arylations. This methodology has shown that the synthesis of thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)‐ or furano[3,4‐c]pyrrole‐4,6‐dione (FPD)‐centred target molecules

  与此相反的传统多步合成，本文中的高效和少数步骤新的合成策略是证明了通过顺序直接C中容易制备的有机电子重要d-π-A-π-d型oligoaryls  ħ芳基化。该方法学表明，以噻吩并[3,4- c ]吡咯-4,6-二酮（TPD）或呋喃并[3,4- c ]吡咯-4,6-二酮（FPD）为中心的目标分子的合成可以从核心结构（受体）或末端结构（供体）经济地步入，这为π功能小分子半导体材料的制备提供了更灵活，更简洁的新合成替代品。另外，检查了合成的低聚芳基的光学和电化学性质。
• Thieno[3,4-<i>c</i>]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors
  作者：Xugang Guo、Rocio Ponce Ortiz、Yan Zheng、Myung-Gil Kim、Shiming Zhang、Yan Hu、Gang Lu、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ja205398u

  日期：2011.8.31

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.